US5210186A - Method for recovery and separation of chitin, proteins and astaxanthin and esters thereof - Google Patents
Method for recovery and separation of chitin, proteins and astaxanthin and esters thereof Download PDFInfo
- Publication number
- US5210186A US5210186A US07/689,767 US68976791A US5210186A US 5210186 A US5210186 A US 5210186A US 68976791 A US68976791 A US 68976791A US 5210186 A US5210186 A US 5210186A
- Authority
- US
- United States
- Prior art keywords
- astaxanthin
- raw material
- phase
- solution
- specific weight
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
- C07C403/24—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by six-membered non-aromatic rings, e.g. beta-carotene
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B61/00—Dyes of natural origin prepared from natural sources, e.g. vegetable sources
Definitions
- the present invention consists of a procedure for the production of astaxanthin and related carotenoids, astaxanthin esters, chitin, proteins and meat. Those products are recovered from plants, algae, bacteria, krill, shrimps and other crayfish and crustacea.
- the method comprises boiling the raw materials in a lye solution to form an alkaline extract and a residue which can be separated by filtration. Typically the alkaline extraction procedure is repeated and the extracts are combined. Upon cooling, the extracts separate into three phases, respectively having a lowest specific weight, an intermediate specific weight and a highest specific weight. The phase having the lowest specific weight upon neutralization yields two phases, the oily phase of which comprises astaxanthin esters.
- the phase with the highest specific weight upon neutralization yields solids consisting of astaxanthin and related carotenoids separable from the neutralized high specific weight phase by filtration.
- the alkaline extract phase having an intermediate specific weight contains protein components from the raw materials. That phase can be neutralized, treated to remove fluoride and heavy metal contaminants and thereafter acidified to precipitate extracted proteins.
- the residue obtained from the original lye solution extraction procedure is dried in concentration formic acid and thereafter dissolved in anhydride formic acid or another strong acid.
- the resulting acidic solution is filtered and diluted with water to precipitate chitin.
- Astaxanthin and related carotenoids are used in the fish farming industry today as dies for colouring the fish meat of species which have red or pale red meat in natural habitats. During cultivation there is no feed that contains enough dye to give this colour flesh to such fish. These dyes are produced today by fermenting algae and synthesizing from a fermentation mixture. This approach is both expensive and time-consuming and necessitates the processing of large volumes of fermentation mixture.
- the present invention describes a procedure which enables astaxanthin and related carotenoids to be produced on an industrial basis much cheaper than with present day technology.
- the present invention is based on the exploitation of natural resources that are unexploitable or which represent a waste disposal problem. These include Antarctic krill; plants, bacteria and algae; and waste from the commercial processing of the meat in species such as shrimps, crayfish and crustacea.
- the present invention also helps to utilize the above-mentioned natural resources better, by using more of the raw material, either by improving the degree of utilization through the production of the required products, or by utilizing the same raw material to produce other types of products.
- the present invention can for example be used to produce astaxanthin and related carotenoids astaxanthin esters, chitin, proteins and meat from Antarctic krill in a way that gives an extremely high degree of utilization of this raw material.
- the shells of Antarctic krill are in addition the greatest unused source of protein in the world. However they cannot be used for feed or food because they contain too many toxic components such as fluorine and toxic heavy metals. With the means of production in the present invention, both the fluorine and the toxic heavy metals can be removed from the shells so that extensive use can be made of the proteins and chitin that can be produced from them.
- the meat is squeezed out behind the cephalothorax using modified shrimp processing equipment. This extraction of the meat must be done within 3 to 4 hours of the time of catching to avoid contamination from the shell, head and cephalothorax which could affect the meat. As the autolysis of krill occurs very quickly and easily, this is another reason why the meat must be extracted within 4 hours of the time of the catch. After the meat has been squeezed out it has to be kept at below 40° C. until it is processed.
- the contaminants in krill are mainly the fluorine in the shell and toxic heavy metals such as cadmium, mercury, lead and zinc. There are high concentrations of cadmium in the cephalothorax and the content of the head.
- krill shell The further treatment of the rest of the krill after the meat has been extracted, i.e., the shell, cephalothorax and the head with its content, here termed krill shell, can take alternative forms.
- the krill shell is boiled in 1.0N NaOH for 30 min. then the extract is separated from the residue.
- the residue is then again boiled in 1.0N NaOH for 30 min. and extract is once more separated from the residue.
- the residue is dried in concentrated formic acid before being dissolved in anhydride formic acid or another strong concentrated acid, filtrated, then water is added to the filtrate to precipitate the purified chitin.
- the extracts from the two boilings are mixed and can either:
- phase with the intermediate specific weight is neutralized by the addition of an acid which causes the formation of two liquid phases, which are separated, and the oily phase which consists of astaxanthin esters is taken care of; where the phase with the highest specific weight is neutralized by an acid, and the solids consisting of astaxanthin and related carotenoids are filtered away and taken care of; and where the phase with the intermediate specific weight is neutralized and has marine oil, Ca 2+ -ions, S 2- -ions and (NH 4 ) 2 HPO 4 for the precipitation of the fluorine and the heavy metal contaminants, where this precipitate is removed from the solution by floating or the equivalent, after this the solution is acidified prior to the precipitation of the purified proteins followed by the separation of these proteins from the solution by filtration or an equivalent method.
- the krill shell is boiled in 0.01N NaOH for 30 min. then the extract is separated from the residue. The residue is then again boiled in 0.01N NaOH for 30 min. and the extract is once more separated from the residue. The residue is then again boiled this time in 1.0N NaOH for 30 min. and the extract is again separated from the residue.
- the residue is dried in concentrated formic acid before being dissolved in anhydride formic acid or another strong concentrated acid, filtrated, then water is added to the filtrate to precipitate the purified chitin.
- the extracts from the first two boilings in 0.01N NaOH are mixed, neutralized and have the addition of marine oil, Ca 2+ -ions, S 2- -ions and (NH 4 ) 2 HPO 4 for the precipitation of the fluorine and the heavy metal contaminants, where this precipitate is removed from the solution by floating or the equivalent, after this the solution is acidified prior to the precipitation of the purified proteins followed by the separation of these proteins from the solution by filtration or an equivalent method.
- the extracts from the last two boilings in 1.0N NaOH are mixed and can either:
- phase with the intermediate specific weight is neutralized by the addition of an acid which causes the formation of two liquid phases, which are separated, and the oily phase consisting of astaxanthin esters is taken care of; where the phase with the highest specific weight is neutralized by an acid and solids consisting of astaxanthin and related carotenoids are filtered away and taken care of; and where the phase with the intermediate specific weight is neutralized and followed by the addition of marine oil, Ca 2+ -ions, S 2- -ions and (NH 4 ) 2 HPO 4 for the precipitation of the fluorine and the heavy metal contaminants, where this precipitate is removed from the solution by floating or the equivalent, after this the solution is acidified prior to the precipitation of the purified proteins followed by the separation of these proteins from the solution by filtration or an equivalent method.
- Astaxanthin can be produced from plants, algae and bacteria that contain this die in accordance with the procedure presented in this patent.
- Plants, algae or bacteria or a mixture of these can be boiled for 30 min. in 1.0N NaOH, after this the extract is separated from the residue of the plants, algae or bacteria and the extract is removed for cooling. During cooling the astaxanthin is separated and is deposited as sediment in the extract.
- the sediment is composed of astaxanthin and extract and these are separated by a known method.
- Shrimps, crayfish and crustacea differ from krill in that they are boiled before the meat is removed for consumption.
- the residue from the shrimps, crayfish and crustacea consists of shell, heads with contents and nonedible components, which can be processed in the same way as krill shell for the production of astaxanthin and related carotenoids, astaxanthin esters, proteins and chitin.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fodder In General (AREA)
- Feed For Specific Animals (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Meat, Egg Or Seafood Products (AREA)
Abstract
Description
Claims (15)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
NO885150A NO176323C (en) | 1988-11-18 | 1988-11-18 | Process for Extraction of Astaxanthin, Related Carotenoids and Astaxanthin Esters from Krill, Shrimp and Other Crustaceans |
NO885150 | 1988-11-18 |
Publications (1)
Publication Number | Publication Date |
---|---|
US5210186A true US5210186A (en) | 1993-05-11 |
Family
ID=19891445
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US07/689,767 Expired - Fee Related US5210186A (en) | 1988-11-18 | 1989-11-15 | Method for recovery and separation of chitin, proteins and astaxanthin and esters thereof |
Country Status (12)
Country | Link |
---|---|
US (1) | US5210186A (en) |
EP (1) | EP0444103B1 (en) |
JP (1) | JP2843669B2 (en) |
AT (1) | ATE205516T1 (en) |
AU (1) | AU635910B2 (en) |
BR (1) | BR8907780A (en) |
DE (1) | DE58909883D1 (en) |
FI (1) | FI98485C (en) |
NO (2) | NO176323C (en) |
OA (1) | OA09497A (en) |
RU (1) | RU2050388C1 (en) |
WO (1) | WO1990005765A1 (en) |
Cited By (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2001077230A2 (en) * | 2000-04-05 | 2001-10-18 | Hafsteinn Helgason | Recovery of compounds using a natural adsorbent |
US6632941B2 (en) | 2001-09-14 | 2003-10-14 | James Wooten | Method of extracting chitin from the shells of exoskeletal animals |
US20040121913A1 (en) * | 2002-12-23 | 2004-06-24 | Freepons Donald Ernest | ''Secondary'' substances found in chitin crustacea shell |
CN100365072C (en) * | 2000-09-25 | 2008-01-30 | 诺维信公司 | Methods for processing crustacean material |
US20090191604A1 (en) * | 2008-01-30 | 2009-07-30 | Bioptik Technology, Inc. | Method for obtaining natural astaxanthin from eggs and gonads of snails |
US20090275745A1 (en) * | 2008-03-19 | 2009-11-05 | Joseph Bristow | Chitosan manufacturing process |
WO2010030193A1 (en) * | 2008-09-12 | 2010-03-18 | Emerald Fisheries As | Process for reducing the fluoride content when producing proteinaceous concentrates from krill |
WO2011023531A2 (en) | 2009-08-28 | 2011-03-03 | Technische Universität Dresden | Two or three-dimensional cleaned chitin skeleton of dictyoceratid sponges, method for the production and use thereof |
CN102106493A (en) * | 2011-01-30 | 2011-06-29 | 大连理工大学 | Method for reclaiming fluoride in Antarctic krill and preparing low-fluorine krill meal |
US8557297B2 (en) | 2008-09-12 | 2013-10-15 | Olympic Seafood, As | Method for processing crustaceans and products thereof |
US8632830B2 (en) | 2003-09-15 | 2014-01-21 | Trouw International B.V. | Fish fodder for freshwater fish and use of such fodder |
CN104003920A (en) * | 2014-06-13 | 2014-08-27 | 华侨大学 | Environment-friendly method for preparing anoxygenic photosynthetic bacterium carotenoids |
US20140242253A1 (en) * | 2002-11-07 | 2014-08-28 | The Texas A&M University System | Process for solubilizing protein |
US8834855B2 (en) | 2005-01-21 | 2014-09-16 | Promar As | Sunscreen compositions comprising carotenoids |
US10499673B2 (en) | 2008-09-12 | 2019-12-10 | Rimfrost Technologies As | Method for processing crustaceans to produce low fluoride/low trimethyl amine products thereof |
US11566137B1 (en) * | 2022-05-30 | 2023-01-31 | Armando Bocobachi Coronado | Method of producing cosmetic skin dye |
US11865143B2 (en) * | 2007-03-28 | 2024-01-09 | Aker Biomarine Antarctic As | Bioeffective krill oil compositions |
Families Citing this family (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB9016012D0 (en) * | 1990-07-20 | 1990-09-05 | Unilever Plc | Pigments |
WO2002000908A2 (en) * | 2000-09-25 | 2002-01-03 | Novozymes A/S | Methods for processing crustacean material |
US8697138B2 (en) | 2007-03-28 | 2014-04-15 | Aker Biomarine As | Methods of using krill oil to treat risk factors for cardiovascular, metabolic, and inflammatory disorders |
US8372812B2 (en) | 2009-02-26 | 2013-02-12 | Aker Biomarine Asa | Phospholipid and protein tablets |
MD132Z (en) * | 2009-09-18 | 2010-12-31 | Институт Микробиологии И Биотехнологии Академии Наук Молдовы | Process for the obtaining of oily astaxanthin preparation |
KR101174474B1 (en) * | 2011-09-28 | 2012-08-22 | 대한민국 | Method of fluoride reduction in krill by extraction solvents |
AU2014203179C1 (en) | 2013-06-14 | 2017-05-04 | Aker Biomarine Antarctic As | Lipid extraction processes |
KR101499199B1 (en) * | 2013-11-04 | 2015-03-09 | 부경대학교 산학협력단 | Manufacturing method of krill oil of low fluorine, low acid value, low peroxide value and high astaxanthin, and krill oil manufactured by the same |
GB201400431D0 (en) | 2014-01-10 | 2014-02-26 | Aker Biomarine As | Phospholipid compositions and their preparation |
NZ735362A (en) | 2015-02-11 | 2019-01-25 | Aker Biomarine Antarctic As | Lipid compositions |
EP3256003B1 (en) | 2015-02-11 | 2022-11-09 | Aker Biomarine Antarctic AS | Lipid extraction processes |
CN106349736A (en) * | 2016-08-05 | 2017-01-25 | 雷春生 | Preparation method of pure organic photosensitive dye |
CN107927738A (en) * | 2017-12-13 | 2018-04-20 | 深圳地天国际生物工程科技有限公司 | A kind of Amti-sanility health-care food and its preparation process |
CN111060468B (en) * | 2020-01-19 | 2022-08-26 | 日照健安检测技术服务有限公司 | Method for rapidly detecting protein content in chitin sample |
Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1224172A (en) * | 1967-06-06 | 1971-03-03 | British Petroleum Co | Improvements in or relating to the production of nitrogenous material |
US3862122A (en) * | 1972-02-16 | 1975-01-21 | Quintin P Peniston | Method of recovering chitosan and other by-products from shellfish waste and the like |
US4119619A (en) * | 1976-12-16 | 1978-10-10 | Sergei Vasilievich Rogozhin | Emulsification method for the processing of kriel to produce protein, lipids and chitin |
US4199496A (en) * | 1974-09-05 | 1980-04-22 | Johnson Edwin L | Process for the recovery of chemicals from the shells of crustacea |
US4293098A (en) * | 1979-04-20 | 1981-10-06 | Systems Consultants, Inc. | Recovery of active chitin and enhanced protein meal |
US4505936A (en) * | 1983-09-14 | 1985-03-19 | Louisiana State University | Process for the utilization of shellfish waste |
WO1986006082A1 (en) * | 1985-04-12 | 1986-10-23 | MATCON RA^oDGIVENDE INGENIO^/RFIRMA A/S | A process for recovering chitin from materials in which chitin occurs together with or connected to proteinaceous substances |
-
1988
- 1988-11-18 NO NO885150A patent/NO176323C/en unknown
-
1989
- 1989-11-15 JP JP2500064A patent/JP2843669B2/en not_active Expired - Lifetime
- 1989-11-15 BR BR898907780A patent/BR8907780A/en unknown
- 1989-11-15 RU SU894895753A patent/RU2050388C1/en active
- 1989-11-15 EP EP89913071A patent/EP0444103B1/en not_active Expired - Lifetime
- 1989-11-15 AU AU46377/89A patent/AU635910B2/en not_active Ceased
- 1989-11-15 DE DE58909883T patent/DE58909883D1/en not_active Expired - Fee Related
- 1989-11-15 WO PCT/NO1989/000119 patent/WO1990005765A1/en active IP Right Grant
- 1989-11-15 AT AT89913071T patent/ATE205516T1/en not_active IP Right Cessation
- 1989-11-15 US US07/689,767 patent/US5210186A/en not_active Expired - Fee Related
-
1991
- 1991-05-15 NO NO911884A patent/NO911884D0/en unknown
- 1991-05-17 OA OA60001A patent/OA09497A/en unknown
- 1991-05-20 FI FI912419A patent/FI98485C/en active
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1224172A (en) * | 1967-06-06 | 1971-03-03 | British Petroleum Co | Improvements in or relating to the production of nitrogenous material |
US3862122A (en) * | 1972-02-16 | 1975-01-21 | Quintin P Peniston | Method of recovering chitosan and other by-products from shellfish waste and the like |
US4199496A (en) * | 1974-09-05 | 1980-04-22 | Johnson Edwin L | Process for the recovery of chemicals from the shells of crustacea |
US4119619A (en) * | 1976-12-16 | 1978-10-10 | Sergei Vasilievich Rogozhin | Emulsification method for the processing of kriel to produce protein, lipids and chitin |
US4293098A (en) * | 1979-04-20 | 1981-10-06 | Systems Consultants, Inc. | Recovery of active chitin and enhanced protein meal |
US4505936A (en) * | 1983-09-14 | 1985-03-19 | Louisiana State University | Process for the utilization of shellfish waste |
WO1986006082A1 (en) * | 1985-04-12 | 1986-10-23 | MATCON RA^oDGIVENDE INGENIO^/RFIRMA A/S | A process for recovering chitin from materials in which chitin occurs together with or connected to proteinaceous substances |
Non-Patent Citations (10)
Title |
---|
"On Ovoverdin, The Carotenoid-Protein Pigment Of The Egg Of The Lobster", K. Stern et al., from the Marine Biological Laboratory, Woods Hole, and the Laboratory of Physiological Chemistry and the Laboratory of Pharmacology and Toxicology, Yale University School of Medicine, New Haven, Oct. 6, 1937, pp. 473-475. |
Chemical Abstracts, K. Stern, et al., "Oververdin, The Carotenoid-Protein Pigment Of The Egg Of The Lobster", vol. 32, 1938, p. 1791. |
Chemical Abstracts, K. Stern, et al., Oververdin, The Carotenoid Protein Pigment Of The Egg Of The Lobster , vol. 32, 1938, p. 1791. * |
Chemical Abstracts, M. Ikeda, et al., "Purification of Chitin From Carapec of Penaeus Japonicus By A Proteolytic Bacterium", vol. 90, 1979, p. 278. |
Chemical Abstracts, M. Ikeda, et al., Purification of Chitin From Carapec of Penaeus Japonicus By A Proteolytic Bacterium , vol. 90, 1979, p. 278. * |
Chemical Abstracts, R. Blumberg, et al., "South African Fish products XXXII. Rock Lobster-Chitin Production From Processing Wastes", vol. 46, 1952, p. 11488. |
Chemical Abstracts, R. Blumberg, et al., South African Fish products XXXII. Rock Lobster Chitin Production From Processing Wastes , vol. 46, 1952, p. 11488. * |
On Ovoverdin, The Carotenoid Protein Pigment Of The Egg Of The Lobster , K. Stern et al., from the Marine Biological Laboratory, Woods Hole, and the Laboratory of Physiological Chemistry and the Laboratory of Pharmacology and Toxicology, Yale University School of Medicine, New Haven, Oct. 6, 1937, pp. 473 475. * |
The Chemistry of Natural Coloring Matters, Fritz Mayer, (Abstract), American Chemical Society Monograph Series, 1943, pp. 66 67. * |
The Chemistry of Natural Coloring Matters, Fritz Mayer, (Abstract), American Chemical Society Monograph Series, 1943, pp. 66-67. |
Cited By (33)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7052721B2 (en) | 2000-04-05 | 2006-05-30 | Hafsteinn Helgason | Recovery of compounds using a natural adsorbent |
WO2001077230A3 (en) * | 2000-04-05 | 2002-06-27 | Hafsteinn Helgason | Recovery of compounds using a natural adsorbent |
US20030118715A1 (en) * | 2000-04-05 | 2003-06-26 | Hafsteinn Helgason | Recovery of compounds using a natural adsorbent |
WO2001077230A2 (en) * | 2000-04-05 | 2001-10-18 | Hafsteinn Helgason | Recovery of compounds using a natural adsorbent |
CN100365072C (en) * | 2000-09-25 | 2008-01-30 | 诺维信公司 | Methods for processing crustacean material |
US6632941B2 (en) | 2001-09-14 | 2003-10-14 | James Wooten | Method of extracting chitin from the shells of exoskeletal animals |
US20140242253A1 (en) * | 2002-11-07 | 2014-08-28 | The Texas A&M University System | Process for solubilizing protein |
US20040121913A1 (en) * | 2002-12-23 | 2004-06-24 | Freepons Donald Ernest | ''Secondary'' substances found in chitin crustacea shell |
US8632830B2 (en) | 2003-09-15 | 2014-01-21 | Trouw International B.V. | Fish fodder for freshwater fish and use of such fodder |
US8834855B2 (en) | 2005-01-21 | 2014-09-16 | Promar As | Sunscreen compositions comprising carotenoids |
US11865143B2 (en) * | 2007-03-28 | 2024-01-09 | Aker Biomarine Antarctic As | Bioeffective krill oil compositions |
US20090191604A1 (en) * | 2008-01-30 | 2009-07-30 | Bioptik Technology, Inc. | Method for obtaining natural astaxanthin from eggs and gonads of snails |
EP2085381A1 (en) | 2008-01-30 | 2009-08-05 | Bioptik Technology, Inc. | Method for obtaining natural astaxanthin from eggs and gonads of snails |
US8030523B2 (en) | 2008-01-30 | 2011-10-04 | Bioptik Technology, Inc. | Method for obtaining natural astaxanthin from eggs and gonads of snails |
US8318913B2 (en) | 2008-03-19 | 2012-11-27 | Agratech International, Inc. | Chitosan manufacturing process |
US20090275745A1 (en) * | 2008-03-19 | 2009-11-05 | Joseph Bristow | Chitosan manufacturing process |
US9480273B2 (en) | 2008-09-12 | 2016-11-01 | Rimfrost As | Reduced flouride crustacean de-oiled protein-phospholipid complex compositions |
US10499673B2 (en) | 2008-09-12 | 2019-12-10 | Rimfrost Technologies As | Method for processing crustaceans to produce low fluoride/low trimethyl amine products thereof |
CN102170795B (en) * | 2008-09-12 | 2014-10-29 | 翡翠渔业公司 | Process for reducing the fluoride content when producing proteinaceous concentrates from krill |
US10701954B2 (en) | 2008-09-12 | 2020-07-07 | Rimfrost Technologies As | Reduced fluorine crustacean polar phospholipid compositions |
US9167832B2 (en) | 2008-09-12 | 2015-10-27 | Emerald Fisheries As | Low flouride crustacean concentrated hydrolysate fraction compositions |
AU2009292317B2 (en) * | 2008-09-12 | 2013-09-12 | Rimfrost Technologies As | Process for reducing the fluoride content when producing proteinaceous concentrates from krill |
US9907321B2 (en) | 2008-09-12 | 2018-03-06 | Rimfrost Technologies As | Separating crustacean polar phospholipid compositions without emulsification |
WO2010030193A1 (en) * | 2008-09-12 | 2010-03-18 | Emerald Fisheries As | Process for reducing the fluoride content when producing proteinaceous concentrates from krill |
US8557297B2 (en) | 2008-09-12 | 2013-10-15 | Olympic Seafood, As | Method for processing crustaceans and products thereof |
US8758829B2 (en) | 2008-09-12 | 2014-06-24 | Emerald Fisheries As | Reduced fluoride content phospholipids/peptide complex meal |
WO2011023531A2 (en) | 2009-08-28 | 2011-03-03 | Technische Universität Dresden | Two or three-dimensional cleaned chitin skeleton of dictyoceratid sponges, method for the production and use thereof |
DE102009028980A1 (en) | 2009-08-28 | 2011-03-03 | Technische Universität Dresden | Two- or three-dimensional purified Chitingerüst of horn sponges, process for its preparation and use |
CN102106493B (en) * | 2011-01-30 | 2012-11-21 | 大连理工大学 | Method for reclaiming fluoride in Antarctic krill and preparing low-fluorine krill meal |
CN102106493A (en) * | 2011-01-30 | 2011-06-29 | 大连理工大学 | Method for reclaiming fluoride in Antarctic krill and preparing low-fluorine krill meal |
CN104003920B (en) * | 2014-06-13 | 2016-01-20 | 华侨大学 | The method of Anoxygenic photosynthetic bacteria carotenoid is prepared in environmental protection |
CN104003920A (en) * | 2014-06-13 | 2014-08-27 | 华侨大学 | Environment-friendly method for preparing anoxygenic photosynthetic bacterium carotenoids |
US11566137B1 (en) * | 2022-05-30 | 2023-01-31 | Armando Bocobachi Coronado | Method of producing cosmetic skin dye |
Also Published As
Publication number | Publication date |
---|---|
NO885150D0 (en) | 1988-11-18 |
WO1990005765A1 (en) | 1990-05-31 |
NO911884D0 (en) | 1991-05-15 |
OA09497A (en) | 1992-11-15 |
JPH04501732A (en) | 1992-03-26 |
EP0444103B1 (en) | 2001-09-12 |
AU635910B2 (en) | 1993-04-08 |
RU2050388C1 (en) | 1995-12-20 |
NO176323B (en) | 1994-12-05 |
EP0444103A1 (en) | 1991-09-04 |
NO911884L (en) | 1990-05-21 |
FI912419A0 (en) | 1991-05-20 |
FI98485C (en) | 1997-07-10 |
BR8907780A (en) | 1991-08-27 |
AU4637789A (en) | 1990-06-12 |
JP2843669B2 (en) | 1999-01-06 |
DE58909883D1 (en) | 2002-01-24 |
NO176323C (en) | 1995-03-15 |
NO885150L (en) | 1990-05-21 |
FI98485B (en) | 1997-03-27 |
ATE205516T1 (en) | 2001-09-15 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US5210186A (en) | Method for recovery and separation of chitin, proteins and astaxanthin and esters thereof | |
US4199496A (en) | Process for the recovery of chemicals from the shells of crustacea | |
US4036993A (en) | Process for preparation of fish meat extracts | |
EP0217887A1 (en) | A process for recovering chitin from materials in which chitin occurs together with or connected to proteinaceous substances | |
US6169217B1 (en) | Method for extracting xanthophylls from corn | |
US4309794A (en) | Method for the separation of fat, pigments and entrail remains from fish raw material | |
DE1289400B (en) | Process for removing undesirable flavors from protein hydrolysates | |
US4387485A (en) | Method of extracting meat of small crustaceans | |
EP0602297A1 (en) | Fish collection and elastin solutions | |
Kristinsson et al. | Chemical processing methods for protein recovery from marine by-products and underutilized fish species | |
US4077950A (en) | Process for the recovery of substantially water-soluble non-toxic protein compounds from fresh non-woody vegetation | |
JP2004208504A (en) | Method for producing astaxanthin-containing yeast extract | |
JP2004026767A (en) | Method for producing phospholipid derived from fish and shellfish | |
RU2207033C2 (en) | Method for wasteless complex reprocessing of chitin-containing raw material | |
Abejón | Seafood processing by-products by membrane processes | |
US3684790A (en) | Method of separating proteins from proteinaceous animal material using mucilage of flax, quince or fleawort | |
JP3022531B2 (en) | How to treat squid softfish | |
SU1275032A1 (en) | Method of producing sea buckthorn oil from press | |
RU2064476C1 (en) | Method of preparing food dye from hydrobionts | |
RU2197836C2 (en) | Method of producing fish feed meal | |
JPH03259063A (en) | Production of seasoning, chitin and glucosamine | |
JP3044008B2 (en) | How to extract fish oil from bonito head | |
DE4417730C1 (en) | Extn. of high value, fat reduced, muscle protein from abattoir meat | |
Katsoulis et al. | Bio-Circular green economy application for the recovery of high value added compounds, such as astaxanthin and glucosamine, from cephalothorax of Karamote shrimp Peneaus kerathurus in Western Greece | |
Lekshmy Nair et al. | Studies on the chemical and nutritional quality of protein powders isolated from shrimp waste |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
FPAY | Fee payment |
Year of fee payment: 4 |
|
FEPP | Fee payment procedure |
Free format text: PAT HLDR NO LONGER CLAIMS SMALL ENT STAT AS INDIV INVENTOR (ORIGINAL EVENT CODE: LSM1); ENTITY STATUS OF PATENT OWNER: LARGE ENTITY |
|
FEPP | Fee payment procedure |
Free format text: PAYOR NUMBER ASSIGNED (ORIGINAL EVENT CODE: ASPN); ENTITY STATUS OF PATENT OWNER: LARGE ENTITY |
|
FPAY | Fee payment |
Year of fee payment: 8 |
|
REMI | Maintenance fee reminder mailed | ||
LAPS | Lapse for failure to pay maintenance fees | ||
LAPS | Lapse for failure to pay maintenance fees |
Free format text: PATENT EXPIRED FOR FAILURE TO PAY MAINTENANCE FEES (ORIGINAL EVENT CODE: EXP.); ENTITY STATUS OF PATENT OWNER: LARGE ENTITY |
|
STCH | Information on status: patent discontinuation |
Free format text: PATENT EXPIRED DUE TO NONPAYMENT OF MAINTENANCE FEES UNDER 37 CFR 1.362 |
|
FP | Lapsed due to failure to pay maintenance fee |
Effective date: 20050511 |